Winter/Spring travel. No min. stay. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this price.

This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.

All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included. Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

Winter/Spring travel. No min. stay. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this price.

This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.

All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included. Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

I fly this trip almost evry weekend for the past two years. Southwest allows me to work in boston and spend my weekends outside of Chicago. 98% of the time we are on time, or early. Southwest is efficent, friendly, economical and a pleasure to fly. I fly enough so I get priority boarding, which I must say is great. Not sure i would be happy getting a high B number and being stuck in a middle seat. Otherwise, hats off to southwest!!

"Southwest does good when flying to Chicago"

reviewed by an Airfarewatchdog Traveler on April 12, 2010

Flight from Boston to Chicago

Airline: Southwest

RT/OW:

Date of Flight: November 2009

Seat Class: economy

Check-in Experience

In-flight Service

Seat Comfort

Overall, the flights to Chicago from Boston and back were nice. Gates were clean with plenty of room for everyone with ample access to food. I'm not typically a big fan of the bulk boarding concept, but the SW team kept us moving and it actually made the process smoother than when I have an assigned seat on other airlines. You better be in the top 20 of the B group if you and your companion want to sure fire way to sit together. Check-in online 24 ahead of time!

Found by other travelers:Boston, MA(BOS)toChicago, IL(MDW)

$844

Flight from Boston to Chicago (BOS - MDW)

Wed, Jun 11 - Thu, Jun 19

Delta

$542

Flight from Boston to Chicago (BOS - MDW)

Thu, Jul 17 - Sat, Jul 19

Delta

$220

Flight from Boston to Chicago (BOS - MDW)

Tue, Oct 21 - Sat, Oct 25

Delta

$451

Flight from Boston to Chicago (BOS - MDW)

Fri, Jul 4 - Mon, Jul 7

Delta

$364

Flight from Boston to Chicago (BOS - MDW)

Thu, Oct 9 - Sun, Oct 12

Delta

$800

Flight from Boston to Chicago (BOS - MDW)

Sat, Jun 7 - Sat, Jun 14

Delta

$460

Flight from Boston to Chicago (BOS - MDW)

Thu, Jul 3 - Sun, Jul 6

Delta

$626

Flight from Boston to Chicago (BOS - MDW)

Fri, Jun 20 - Sun, Jun 22

Delta

$475

Flight from Boston to Chicago (BOS - MDW)

Fri, Jul 4 - Sun, Jul 13

Delta

$401

Flight from Boston to Chicago (BOS - MDW)

Tue, Jul 15 - Thu, Jul 17

Delta

There are approximately 20 flights covering the route from Logan International Airport in Boston to Midway Airport in Chicago, provided by as many as 2 airlines.

The following airlines often offer cheap flights from Boston to Chicago